HCID 70979845, compound → HCID 70980495, compound

HRID 1749110Notes

Reaction equation

HRID 1749110 reaction equation
C(O[C:6](=O)[N:7]([CH:9]([C:11](=[O:31])[NH:12][C:13]1[N:18]=[C:17]2[N:19]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=3)[C:20](=[O:22])[NH:21][C:16]2=[CH:15][CH:14]=1)[CH3:10])C)(C)(C)C>CO.[Pd]>[ClH:30].[ClH:30].[CH2:23]([N:19]1[C:17]2=[N:18][C:13]([NH:12][C:11](=[O:31])[CH:9]([NH:7][CH3:6])[CH3:10])=[CH:14][CH:15]=[C:16]2[NH:21][C:20]1=[O:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 1

HCID 70979845HCID 70979845, compound

Product 2

HCID 313Hydrochloric AcidHCID 70980495HCID 70980495, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

{1-[3-(4-Chloro-benzyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-5-ylcarbamoyl]ethyl}-methyl-carbamic acid tert-butyl ester (100 mg, 0.22 mmol) (Example 1, product from Step 4) was dissolved in MeOH and stirred with Pd/C (50 mg) under hydrogen for 16 hours. The solution was filtered and evaporated in vacuo. Treatment with HCl (in an analogous fashion to General procedure 3) gave the title compound (38 mg) as a white solid. 1H NMR (400 MHz, DMSO-d6): 11.26 (1H, s), 10.86 (1H, s), 9.50 (1H, s), 9.03 (1H, s), 7.78 (1H, d), 7.42 (1H, d), 7.37-7.22 (5H, m), 5.01 (2H, s), 4.06-3.95 (1H, m), 2.55-2.52 (3H, m), 1.48 (3H, d). MS: [M+H]+=326.

Workup

  1. filtrationThe solution was filtered
  2. customevaporated in vacuo

Sources & evidence

ORD record
ord-ad503cfc5e66432a96acd78e7b7de48e
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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